1430399-10-2Relevant academic research and scientific papers
Design of glycosyltransferase inhibitors: Pyridine as a pyrophosphate surrogate
Wang, Shuai,Cuesta-Seijo, Jose A.,Lafont, Dominique,Palcic, Monica M.,Vidal, Sebastien
, p. 15346 - 15357 (2013)
A series of ten glycosyltransferase inhibitors has been designed and synthesized by using pyridine as a pyrophosphate surrogate. The series was prepared by conjugation of carbohydrate, pyridine, and nucleoside building blocks by using a combination of gly
Glycosylation of 'basic' alcohols: Methyl 6-(hydroxymethyl)picolinate as a case study
Wang, Shuai,Lafont, Dominique,Rahkila, Jani,Picod, Benjamin,Leino, Reko,Vidal, Sébastien
, p. 35 - 46 (2013/05/21)
Glycosylation is promoted by acid promoters rendering the reactions with basic acceptors challenging. This report presents an in depth study involving methyl 6-(hydroxymethyl)picolinate as the model acceptor and 22 glycosyl donors to afford the desired glycosides in good yields ranging from 46% to 85%. Several parameters were evaluated, including the protecting groups of the glycosyl donor, the leaving group at the anomeric center, and the promoter. The influence of the pyridine ring was evident with a benzene-based acceptor affording high yields of glycoside (79%) in comparison to the pyridine-based acceptor (46%). The present work provides a general and reliable access to pyridine-containing glycosides.
